Preheat your oven to 400°F and line a large baking sheet with parchment paper.
Toss the cubed butternut squash, apple slices, onion, and garlic cloves with olive oil, sea salt, and black pepper directly on the sheet.
Roast the vegetables for 25 to 30 minutes until the squash is fork-tender and the edges are slightly caramelized.
While the vegetables roast, pan-sear the chicken breast over medium heat until cooked through, then shred it into small pieces using two forks.
Transfer the roasted squash, apple, onion, and peeled garlic into a high-speed blender.
Add the chicken bone broth, ground cinnamon, and fresh sage to the blender and process until the mixture is completely smooth and creamy.
Pour the soup into a medium pot, stir in the shredded chicken, and simmer over medium-low heat for 5 minutes to meld the flavors before serving.